26: How to Sell the Same Company Twice — And Exit With More Every Time
Matthew Porter, Partner & Co-Founder at EONOVA
In this episode of From Angel to Exit, host Bruce Eckfeldt welcomes Matthew Porter, founder and former CEO of Contegix, for a deep dive into what it takes to navigate private equity exits as a founder-CEO.
Matthew bootstrapped Contegix into a fast-growing managed infrastructure company, eventually attracting interest from private equity buyers. The first sale gave him valuable lessons about negotiating control, earnouts, and cultural alignment. But it was the second sale—after a strategic roll-up and operational scaling—that delivered a more intentional, better-structured exit.
He shares what it’s like to go from a small team to 200+ employees, the challenges of transitioning out as a founder, and the importance of maintaining optionality in your deal terms. Now at EONOVa, Matthew is building again—applying everything he learned from both exits to help build high-performance, cloud-native companies with scalability and founder alignment at the core.
Throughout the episode, he emphasizes founder identity, mental clarity, and the value of long-term thinking when it comes to M&A. His insights are real, actionable, and speak directly to any founder navigating their first—or second—exit.
Key Takeaways
You can sell your company twice—if you structure the first exit with a second in mind.
Founder identity and mental health are critical in long-term exit strategy.
Private equity isn’t the enemy—but you must understand their value model.
Second exits offer a rare chance to fix what you missed the first time.
Growth through acquisition drives both scale and valuation.
Negotiate your role, not just your price, post-exit.
Build with optionality: prepare for a sale, even if you’re not planning one.
Fit and alignment often matter more than the highest bidder.
Contact Information:
Email: mporter@enova.co
https://www.linkedin.com/in/meporter/
